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Related Concept Videos

Strong Acid and Base Solutions03:22

Strong Acid and Base Solutions

A strong acid is a compound that dissociates completely in an aqueous solution and produces a concentration of hydronium ions equal to the initial concentration of acid. For example, 0.20 M hydrobromic acid will dissociate completely in water and produces 0.20 M of hydronium ions and 0.20 M of bromide ions.
Weak Base Solutions03:21

Weak Base Solutions

Some compounds produce hydroxide ions when dissolved by chemically reacting with water molecules. In all cases, these compounds react only partially and so are classified as weak bases. These types of compounds are also abundant in nature and important commodities in various technologies. For example, global production of the weak base ammonia is typically well over 100 metric tons annually, being widely used as an agricultural fertilizer, a raw material for chemical synthesis of other...
Polyprotic Acids03:38

Polyprotic Acids

Acids are classified by the number of protons per molecule that they can give up in a reaction. Acids such as HCl, HNO3, and HCN that contain one ionizable hydrogen atom in each molecule are called monoprotic acids. Their reactions with water are:
Buffers02:56

Buffers

A solution containing appreciable amounts of a weak conjugate acid-base pair is called a buffer solution, or a buffer. Buffer solutions resist a change in pH when small amounts of a strong acid or a strong base are added. A solution of acetic acid and sodium acetate is an example of a buffer that consists of a weak acid and its salt: CH3COOH (aq) + CH3COONa (aq). An example of a buffer that consists of a weak base and its salt is a solution of ammonia and ammonium chloride: NH3 (aq) + NH4Cl...
Titration Calculations: Weak Acid - Strong Base03:55

Titration Calculations: Weak Acid - Strong Base

Calculating pH for Titration Solutions: Weak Acid/Strong Base
For the titration of 25.00 mL of 0.100 M CH3CO2H with 0.100 M NaOH, the reaction can be represented as:
Acid and Bases: Ka, pKa, and Relative Strengths02:35

Acid and Bases: Ka, pKa, and Relative Strengths

This lesson delves into a critical aspect of the relative strengths of acids and bases. The strength of an acid is evaluated by the acid dissociation into its conjugate base and a hydronium ion in water. The complete dissociation of a strong acid is confirmed with a very high concentration of hydronium ions. As a result, an incomplete dissociation process affirms a weak acid. Therefore, the equilibrium is in the forward direction for strong acids and backward for weak acids in these reactions.

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Determination of the Gas-phase Acidities of Oligopeptides
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Estimating pKa values for pentaoxyphosphoranes.

J E Davies1, N L Doltsinis, A J Kirby

  • 1University Chemical Laboratory, Cambridge Uiversity, Cambridge CB2 1EW, United Kingdom.

Journal of the American Chemical Society
|June 6, 2002
PubMed
Summary
This summary is machine-generated.

This study estimates pKa values for hydroxyphosphoranes using two distinct methods. Results show significant differences between apical and equatorial hydroxyl group ionizations, crucial for understanding phosphorane chemistry.

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Area of Science:

  • Organophosphorus Chemistry
  • Computational Chemistry
  • Physical Chemistry

Background:

  • Hydroxyphosphoranes are key intermediates in phosphorus chemistry.
  • Understanding their ionization behavior (pKa) is essential for predicting reactivity.
  • Existing methods for pKa estimation in these systems are limited.

Purpose of the Study:

  • To independently estimate pKa values for apical and equatorial hydroxyl groups in hydroxyphosphoranes.
  • To compare the accuracy and applicability of two different computational methods for pKa determination.
  • To provide reliable pKa data for representative hydroxyphosphorane structures.

Main Methods:

  • Utilized a bond length-pKa correlation derived from crystal structures of cyclohexanol derivatives.
  • Employed ab initio molecular dynamics calculations for pKa estimation.
  • Applied both methods to specific hydroxyphosphorane examples: tetracyclohexyloxyhydroxyphosphorane and pentahydroxyphosphorane.

Main Results:

  • The bond length-pKa method yielded pKa values of 13.5 ± 1.5 (apical) and 8.62 ± 1.87 (equatorial) for tetracyclohexyloxyhydroxyphosphorane.
  • Ab initio molecular dynamics calculations provided pKa values of 14.2 (apical) and 9.8 (equatorial) for pentahydroxyphosphorane.
  • Both methods indicated a significant difference in acidity between apical and equatorial hydroxyl groups.

Conclusions:

  • Two independent computational methods provide consistent, albeit slightly different, pKa estimates for hydroxyphosphorane ionizations.
  • The findings highlight the importance of hydroxyl group position (apical vs. equatorial) in determining phosphorane acidity.
  • This work offers valuable pKa data for advancing the study of organophosphorus compounds.